Chemical Properties
white to off-white crystalline needles or powder
Uses
2,6-Diacetylpyridine is used as intermediate in organic synthesis. It is a precursor to ligands in coordination chemistry.
Application
2,6-Diacetylpyridine can be used as a starting material for the synthesis of:
Iron and cobalt bis(imino)pyridyl complexes, catalysts for ethylene oligomerization.
Thiosemicarbazone derivatives with potential application as anti-mycobacterial tuberculosis agent.
Macrocyclic pentadentate nitrogen–sulphur donor ligands by [1+1] condensation with 1,2-di(o-aminophenylthio)ethane.
Synthesis
The general procedure for the synthesis of 2,6-diacetylpyridine from 2,6-diethylpyridine was as follows: 1.0 equiv. of N-hydroxyphthalimide (NHPI) was added to a 25 mL Schlenk reaction tube and dried under vacuum for 15 min. Subsequently, acetonitrile was added as a solvent under oxygen atmosphere, followed by 2.0 equivalents of tert-butyl nitrite and 0.5 mmol of 2,6-diethylpyridine. After sealing the reaction tube with a polytetrafluoroethylene plug, it was immersed in an oil bath preheated to 90°C for 36 hours. After completion of the reaction, the solvent acetonitrile was removed by distillation under reduced pressure. The crude product was purified by column chromatography with the eluent being petroleum ether/ethyl acetate (5:1, v/v) to give 2,6-diacetylpyridine. The product was a yellow solid in 54% yield.
References
[1] Patent: CN107011133, 2017, A. Location in patent: Paragraph 0120; 0121; 0124; 0125
[2] Organic Letters, 2017, vol. 19, # 20, p. 5593 - 5596
[3] Patent: US9266982, 2016, B2. Location in patent: Page/Page column 34
